Tributylvinyltin → HCID 68713053, compound

HRID 1159764Notes

Reaction equation

HRID 1159764 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])(=[O:13])=[O:12].[CH2:21]([Sn](CCCC)(CCCC)C=C)[CH2:22]CC>CC#N>[CH3:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:11]([N:6]1[C:7]2[C:3](=[C:2]([CH:21]=[CH2:22])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 220153344-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole2×

Product 1

HCID 68713053HCID 68713053, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromo-1-[(2-methylphenyl)sulfonyl]-1H-indole (500 mg, 1.43 mmol; Intermediate 14) was dissolved in dry MeCN (8 mL) and distributed into two microwave vials. Tributyl(vinyl)stannane (0.417 mL, 1.43 mmol) and Pd(PPh3)2OAc2 (27 mg, 0.036 mmol) was added to each vial. The reaction mixtures were irradiated with microwaves at 180° C. for 720 s. The mixtures were combined, filtered and concentrated. Purification was performed by flash chromatography (30% hexane in DCM). This afforded the product (300 mg, 71%) as a yellow sticky oil. MS (ESI+) for C17H15NO2S m/z 298 (M+H)+.

Workup

  1. customThe reaction mixtures
  2. customwere irradiated with microwaves at 180° C. for 720 s
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-7173c000c8294f19906d8f0881d06add
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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